p-Toluenesulfonic acid → 7-Bromo-6-fluoro-1H-indene

HRID 536464Notes

Reaction equation

HRID 536464 reaction equation
[Br:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH:6]2O.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]=[CH:6]2

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 89621428HCID 89621428, compound

Product 1

HCID 684592997-Bromo-6-fluoro-1H-indeneYield 79%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of Example 25B (923 mg, 3.99 mmol) and TsOH (45.6 mg, 0.240 mmol) in toluene (20 mL) was heated to reflux for 2 hours. The mixture was cooled to ambient temperature and was then concentrated under reduced pressure. The residue was passed through a silica gel frit to provide the title compound (670 mg, 3.14 mmol, 79%). MS (DCI) m/z 231 (M+NH4)+.

Workup

  1. temperatureto reflux for 2 hours
  2. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-d643f7a16fde4a659b360fa02e717712
Source dataset
uspto-grants-2014_10
Patent number
US08859584B2

Reaction notes

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